This article examines the educational experiences of undocumented high school students during the Trump administration--a time marked by the intensification and expansion of immigration enforcement practices. Drawing on 24 in-depth interviews, we find that undocumented high school students experienced increased instances of bullying near the time of the 2016 U.S. presidential elections. Our respondents also worried about the growing uncertainty surrounding immigration policies and the future of DACA. This uncertainty shaped their plans; many students felt compelled to prioritize working and delay starting college to make use of their work permit while they had access to DACA and build emergency savings. While the current political climate gravely exacerbated students' fear and anxiety, students demonstrated a tremendous amount of resiliency, agency, and determination to achieve their goals. We find that access to a support network and encouraging school personnel played a key role. Thus, we conclude this article with a set of key recommendations for educators and counselors who are working with undocumented students and their families on the ground. [Additional funding for this project was provided by North County Higher Education Alliance, Latino Center for Leadership Development, the Sociological Initiatives Foundation, National Latino Research Center, and UndocuScholars at UCLA.]